Updated on 03.03.08

Learning the Right Lessons from Your Mistakes

Trent Hamm

All of us regularly make mistakes in our lives – choices that seem like the right ones at the time, but later turn out to have been poor choices. This is true for all avenues of life: our careers, our personal lives, our finance choices, and anything else where we make decisions and have to live with the consequences.

I’m no exception to this. I can think of countless times, even quite recently, where I made what seemed like a completely appropriate and correct choice, only to discover later that it wasn’t. One example that immediately came to mind was my decision to write about personal hygiene from a factual “here’s what you do” perspective. Instead, as I later discovered, I could have made the same points without seeming condescending by instead describing the reasons why personal hygiene is important.

What follows are some of the steps you can take to not only identify your actual misstep, but to take appropriate lessons from it and apply them to your life.

Be open and willing to realize that you have in fact made a mistake.
The first step towards utilizing a mistake to improve yourself is to realize that you’ve made a mistake at all. Quite often, it’s not clear that you’ve even made a mistake – you might believe that your plan is well crafted and well considered and that a bad result is the result of things outside your control. Or, you might believe that the response of others is completely outside of what’s reasonable.

Whenever you get a poor outcome, the first place to look for blame is yourself. Almost always, there is some aspect of your plan that went awry, some piece that you could have done differently, some preparation you could have made. Even when the blame seems obviously in someone else’s court, there’s still often something you could have done to soften the blow.

Not too long ago, I gave a speech at a convention. I was extremely well prepared for it and the talk itself went fine. What I didn’t expect, however, was the question and answer session afterwards. Instead of absorbing more of the material, I had spent much of my time really nailing the talk – and thus I was eaten alive by the questioners. Immediately afterwards, I was angry at the questioners – where did they come up with this stuff? In the end, though, I saw that the real blame lay with myself – that I had made a mistake in not finding out more about the venue in advance.

Dig down until you can figure out the core of the incorrect choice you made.
Sometimes, you’ll look at a bad outcome and be completely unable to see how it could possibly be your fault. It’s very easy to fall into the trap of laying blame on external sources instead of ourselves – it spares our own feelings and gives us a target to vent at.

It’s especially easy to do this when the mistake you made isn’t obvious at first glance. Give it time. Dig through all of your assumptions and find out which one was wrong. If you didn’t find it the first time, dig through them again. Dig through the ideas that made up your assumptions. Eventually, you will find a mistake that you made.

One of the experiences of my childhood that really shaped how I viewed money and entrepreneurship came when I was about ten years old. I collected aluminum cans for several months, intending to sell them at a great profit, but on the day of the sale, the cans were stolen from me by someone I trusted. It’s very easy to blame the thief here, and it’s something I did for a long time. However, when I dig deep into that experience, I realize that some of the blame is my own – I didn’t secure the cans well at all. It would have been trivial to just lock the door, but I didn’t bother to do it.

Identify the reasons you used to make that incorrect choice.
Once you’ve figured out the incorrect choice you’ve made, it’s easy to say, “Well, I won’t do it that way again!” That’s still the easy path, though.

Why did you make that choice to begin with? What were your reasons for making that choice? It’s quite likely that your mistake was just one piece of a larger pattern, one worth investigating in detail.

When I left that door unlocked, it wasn’t just that I didn’t think to lock a door. It was a sign that I wasn’t careful about my things, that I was lacking in the proper care and respect for the items that were important to me. This was true for a lot of my life – I’d leave important stuff just lying around, not really caring for or respecting it or keeping it safe.

Construct a plan to address those flaws.
Once you’ve figured out the underlying issue, what are you going to do about it? You’ve done the legwork to uncover some aspect of yourself that really needs some work, so you’re going to need a plan to deal with it.

If you’re trying to overcome a bad habit or a psychological block, it might be useful to develop a daily plan for addressing that issue. Is there something you can do or practice every day that will gradually lead you to a different path?

Take, for example, the issue of the slovenly individual discussed recently in the hygiene postings. If a person realizes that people are being driven away by unsanitary behavior, it might actually be worthwhile for that person to actually develop and write out a daily hygiene routine – bathing, washing hair, brushing, flossing, and so on.

What about my own issues with caring for my stuff? I actually started a daily routine of just picking up after myself, putting items back where they should be, and making sure that things are cared for and protected. It’s something that, over time, is becoming very natural to me – I find myself picking things up almost routinely that I would have just not worried about before.

Share that plan with others.
Before you go off implementing this plan you thought up, talk about the whole thing with a few people that are very close to you who are willing to offer honest feedback. It is very easy to radicalize a solution, and that itself can be dangerous.

Move through each step of your logic with someone close to you and ask for their honest input. It may be that you’re barking up the wrong tree entirely with the problem, or it may be that your solution is too weak – or too fierce – to really help with the problem. Listen and take into account what these people tell you.

Whenever I’m figuring out a way to improve myself, the first person I discuss it with is my wife. She’s always willing to offer excellent feedback to me, and our relationship is such that neither one of us pulls punches with commentary. I trust her on a very deep level – she knows me incredibly well and often has better insights into my thoughts than I do.

If you have someone in your life like that, talk to them. Share your mistakes and work with that person to make sure that you don’t make another mistake via your solution.

The first step, though, is up to you. Are you ready to take it?

Loading Disqus Comments ...
Loading Facebook Comments ...
  1. Saving Freak says:

    The best advice in here is talking to your wife/spouse. No matter how we try to slice things men and women are different and see things very differently. When I get a negative response from people I ask my wife how I could have approached things better. She always has a different perspective than I do and it has always been helpful in me learning how to handle a situation differently.

  2. Cat-Daddy says:

    Very important in money management, especially stock investing. Being able to step back and look at things objective is quite hard, but if you can do it, you may see that you’re irrationally in love with a loser of a stock that you should just dump. But thanks for keeping it less on money this time and more on personal responsibility– reading this is certainly cheaper than therapy! The only person I can change is myself, after all.

  3. Joe says:

    Given that you talk about addressing mistakes, it is suprising that you are so reluctant to go the mea culpa route. Reread your response to the comments – you never apologized for the tone of the article, instead you simply rationalized what you wrote…

  4. Joe says:

    Given that you talk about addressing mistakes, it is suprising that you are so reluctant to go the mea culpa route. Reread your response to the comments in the personal hygiene post – you never apologized for the tone of the article, instead you simply rationalized what you wrote…

  5. Trent Hamm Trent says:

    … uhm, the entire point of this article is that it’s my fault. I made the mistake of offering overly simplistic instruction without really explaining why, meaning that I wound up talking down to my audience when I didn’t intend to. That’s exactly what the commenters called me on. I’m not sure what you’re saying beyond that, Joe.

  6. Cat-Daddy says:

    I’m not sure either, Trent.

    Maybe that no matter what you do some people won’t be satisfied? (The appearance of relative) success makes you a target, I guess.

  7. Tom Hemming says:

    I’ve generally enjoyed reading what you had to say but have some hessitation with this post. While I agree there can be unhealthy patterns to our choice making process that should be examined over examination can, I believe, lead to a pattern of not making any choices due to fear of any choice being the wrong one. I believe that when faced with a choice, short of shooting yourself in the foot or not, you should consider the idea(s) that lead to the point of choice as having a potentially positive outcome. You should gather as much information as needed to help you make the jump. Hopefully you’ve done your homework enough to make as fully an informed decision as possible then jump. The outcome may be positive or maybe not. There are many variables which can affect the outcome many of which are out of sight no matter how hard you look. If the outcome is not what you hoped after following a good process……… You tried don’t beat yourself up to much. Life is full of unknowns and unseeables. When Gorbashof left office he told a story about a young monarch who when faced with the need to make a decision sent a thousand experts in search of the information needed to help him/her make the decesion then proceeded to spend the rest of his/her life waitning for all the information to come back. Moral was make your decision based on the best information you have available to you at the time and hope for the best. Then go on living which ever way it goes.

  8. Jae says:

    Trent, your willingness to look at where you missed the mark in the hygiene article is admirable. We all make mistakes. It’s what we do with the subsequent lessons that help us grow.

    Joe, Trent did rationalize his posts to his readers in his comments. However, in this article, he reflected and admitted his mistakes. Very admirable.

    You have really listened to your readers, and reflected. You are going far!

  9. Eric C says:

    Forgive me if this quasi-political comment is too inappropriate for this website but…our current President, Mr. George W. Bush would do well to read this article.

    Another fine piece of writing Trent, if I do say so myself.

  10. eaufraiche703 says:


    I DON’T agree about the hygiene article!

    As a teacher, an avid reader of books on self help, and a former secretary to a widely syndicated advice columnist, I must say that one should make no assumptions re: the personal grooming habits of others.

    If one had unsuccessfully attempted to advance in one’s field and had other parts of the equation in place, one might reflect upon grooming concerns if given the opportunity (reading your column)…

    You’ve probably imroved the odds that countless people will achieve success w/ the hygiene discussion.

    Jeez, Joe…. lighten up!

  11. Kacper says:

    I like this approach. I can share you one advice, that is helpful to start admitting own mistakes and analyzing them.

    Play chess. This is a game of mistakes. When you are losing, you can get frustrated on luck or your opponent. But in the end, you lost because of your mistake(s). Analyze the game and find out what you could do better.

    After some time of playing chess, it is easier to see the analogy between it and your life. You simply develop a habit of admitting to your mistakes and looking how you could perform better to avoid it.

    Playing chess is also a great exercise for your mind as well as very entertaining. Why not to try?

  12. Frugal Dad says:

    Few are willing to own their mistakes, especially in public. I admire the fact that you are man enough to do that when the time calls for it (personally, I didn’t get a condescending tone from your hygiene article – but then again, I am pretty thick-skinned and direct in my own communications).

    My wife also has a knack for keeping me on track. You know those amusement park rides with the old cars that you can “drive” leisurely around a track, but they are guided by a center rail so you can’t go too far to the right, or too far to the left? That center rail is my wife. She keeps me from going off on one of my wild entrepreneurial tangents, keeping me on track. Occasionally, I’ll steer her a little off center, and that give and take provides the balance needed for a great relationship.

  13. clevelis says:

    I agree. Being able to make mistakes and learn from them has helped me be a “better” risk taker. By this I mean that I feel more free to try new things and not be ruled by fear or “what if’s”. Of course, this does not take the place of wisdom, common sense and such…

  14. Trent Hamm Trent says:

    “personally, I didn’t get a condescending tone from your hygiene article – but then again, I am pretty thick-skinned and direct in my own communications”

    So am I. I usually try to be very direct and when I see a negative comment, I usually think that somehow I’ve just failed to communicate a point. It often takes stepping back and doing analysis like this to see that I’ve done something else wrong, usually something more fundamental.

  15. SJean says:

    I really appreciate the willingness to admit your mistake, even if it is just in the articles tone. I find that is something that you are a little weak in–people criticize and you are quick to rationalize why you were right. Thank you for proiving me wrong!

  16. I would like to applaud you for just throwing this out there. Keeping an open mind is definitely something to always consider, as well as understanding things will not always come across as planned.

    Honesty is always appreciated :)

  17. Louie says:

    i dont really agree with this entire post trent. On the whole yes, it is very vital to accept responsibility for one’s mistake, but also it is easy to become a chronic problem to consistently take the “responsibility” for a mistake. Personally i do this all the time when something goes wrong i think of a million reasons that i “shoulda woulda coulda” and when it really boils down to it, it was something completely out of the sphere of my “control.” learning how to not accept a mistake as yours is just as crucial as taking responsibility.

  18. Brent says:

    I did not see anything wrong with your personal hygiene articles either. Part of me thinks that if you can not give adults the benifit of the doubt, you should not speak with adults. People will complain about anything if you give them the shot, too. If you were to map out peoples objects to the rhetorical maps, you will see that many of those objections are on the Pathos level. I don’t think I have to go further to explain the objection to that type of argument.

  19. Brent says:

    I guess a more ‘direct’ way of saying what I did in my previous post would be, “Be a man and own up to your sins, make restitution, and remember that there is a reason why the phrase ‘Goto Hell.’ exists”

  20. Ria Kennedy says:

    This is very timely and I appreciate it. Thank you.

  21. Trent Hamm Trent says:

    The Simple Dollar regularly generates discussion in areas that I would have never believed before I started it. This is a good thing.

  22. Blaming oneself is okay in terms of promoting humility and self accountability, but one shouldn’t resort to self deprecation right off the bat.

    Maybe it’s my legal background but I always find myself defending the validity of my position first and promptly attributing and shifting blame and causation to other parties. Force of training and habit.

  23. Sandy says:

    I agree w/Joe – you rationalized and defended yourself, and didn’t apologize, and as a result came across as being very self-serving and self-righteous in that other article. If you meant to address the minority, as you stated in your comments, it wasn’t stated in your article, and so a “I apologize for offending the majority of my readers; I was trying to reach a minority…” statement would have sufficed. The thing I’ve learned about writing is that sometimes when we write, we hold thoughts in our head because we assume that those thoughts are so obvious that they are a given, and then later, when we receive feedback from many readers, we realize that we should have spelled those thoughts out on paper, because for some readers, they weren’t obvious or a given. This has happened to me too sometimes when I write, and then someone calls me on something I neglected to mention and like you, I was so surprised because I thought everyone had the same thoughts in their head like I do — some do, some don’t! There are some things that are so obvious to many, but not to others. Water under the bridge, life moves on – you’re a good guy, we all know that.

  24. Jillian says:

    I agree with Tom. My husband is one of those people who avoids making important choices for fear of being wrong. It holds him back in so many ways, and I hate watching all his potential wasting away while he tries to convince himself he’s happy where he is.

    You have to balance the introspection against the knowledge that sh*t happens and you can’t control everything. I think learning to use a ‘failed’ outcome to your advantage is more important that endlessly questioning what you could have done better.

  25. Linda says:

    I thought your article on hygene was right on target. Most of us know what you stated, but I personally have tended to get a little relaxed as now I am not going into a 9 to 5 job every day. It made me see that our self esteem can be linked in some ways to our grooming.

    I have also noticed that when some people come under a lot of pressure or begin getting depressed, it may show up in their grooming.

    Another part of the article I thought was right on target was the part about the work dress code and dressing on the high end instead of the low end of your company’s dress standard. I know for a fact that if this advice is taken, it will play a role in the speed a person advances.

    Trent, don’t change your style because a few people are offended or critical. It is a very small percentage of your readers and the rest of us LOVE what you are doing. Even those who criticize you are devoted readers. You are doing a great job.

    Can’t wait to purchase your book. Let us know when it becomes available for pre-purchase.


  26. Maranda says:

    Hey Trent! I just wanted to tell you that I feel like your articles and getting deeper and deeper and deeper…What happened to simple. When I first starting reading, I was really impressed. These were things that I could use, practical everyday advice for the home. Now…it’s like advice for running a business and blah blah blah! Please keep it simple, as in SIMPLE Dollar. Thanks a bunch!

  27. Crystal says:


    People grow with their blogs! If The Simple Dollar is no longer a good fit, there are hundreds of other personal finance blogs out there. Maybe you could even start one of your own!

  28. Chris says:


    You are right!!! I am out of here!!!!

  29. Noting is a mistake, its just unexpected / unanticipated to its full glory. We need to move on ongrowthtrack

  30. 1hard1 says:

    You can’t candy-coat your thoughts/opinions to suit everyones own comfort zones. Likewise, you have the right to look back on your thoughts of where you are at the present and see the slight differences as to where you were in your yesteryear. I appreciate that you choose not to be purposefully offensive or completely useless with your shared thoughts. You have not said anything deserving of harsh ridicule. Agree to disagree, and let’s continue to open each others’ minds to other perspectives.

  31. daydreamr says:

    You certainly can’t please everyone and I’m amazed that people are still harping on the hygene issue. Why is this still an issue? It didn’t bother or offend me in any way. I am a very clean and hygene-concious person. I know how to bathe but still, I didn’t feel it was condescending at all. I would not consider it to be a mistake. I don’t think that it’s necisary for you to clarify anything or apologize to the offended readers. they are being overly critical and I’m sure it has a lot to do with their own insecurities. If I were in your situation, I would tell these readers that, if they can’t take an article for what it is, they don’t have to read your blog. You should be comended, Trent, for trying to reach everyone and having a diverse approach to your blog. I read your articles just about every day and some of the material doesn’t apply to me and, sometimes it doesn’t peak my interest so I skim thru it and move on. But I can relate to your point that there are many people who just don’t know how to clean themselves or their homes. I was just trying to discuss this with an older man, about 50. Very gross, unkempt appearance does not go over well in society. It doesn’t impact the way I view him (for the most part) but people think I’m weird for associating w/him. As for learning from your mistakes, every thing that happens is an opportunity to learn a lesson. You can’t beat yourself up over things that were out of your control, bad circumstances, or poor decision making. You certainly can benefit from analyzing the situation and applying the lessons learned to the future. It also has a lot to do with forgiveness. Like the cousin who stole Trent’s cans, it takes a lot to do this but in the end, you can be the bigger person. Forgive others for their transgressions but don’t forget. Live and learn because life goes on…

Leave a Reply

Your email address will not be published. Required fields are marked *